The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-c]pyridine derivatives, possessing anti-inflammatory activity.
Vladimir P Zaytsev, Daria N Simakova, Viktoria S Maslova, Valentina V Ilyushenkova, Roman A Novikov, Mikhail S Grigoriev, Roman D Danilov, Roman Litvinov, Irina A Kolesnik, Vladimir I Potkin, Fedor I Zubkov
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引用次数: 0
Abstract
An unexpected cascade of N-acylation/intramolecular [4 + 2] cycloaddition/decarboxylation/isoxazole ring-opening reactions is observed in the course of the interaction between 3-(isoxazol-3-yl)allylamines and maleic or trifluoromethylmaleic anhydrides. This four-step sequence begins with the initial N-acylation of allylamines by the anhydride, followed by an intramolecular Diels-Alder reaction, which is accompanied by spontaneous decarboxylation, and ends with the opening of the isoxazole ring. As a result, an original approach to a pyrrolo[3,4-c]pyridine core was discovered. A test series of pyrrolo[3,4-c]pyridin-3-ones was investigated for anti-inflammatory activity and cytotoxicity, including the ability to inhibit NLRP3 inflammasome activation.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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